In order to obtain constrained analogues of tryptophane, five-membered lactams and lactones bearing 4-indolyl and 3-carboxylic groups were prepared in a completely diastereoselective manner, resulting in a trans relationship. Furthermore, the use of chiral precursors in the synthesis yielded enantiomerically pure compounds with three contiguous chiral centres. © 2000 Elsevier Science Ltd.
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